JP2865698B2 - イホスフアミド‐メスナ凍結乾燥調製物及びその製法 - Google Patents
イホスフアミド‐メスナ凍結乾燥調製物及びその製法Info
- Publication number
- JP2865698B2 JP2865698B2 JP1066489A JP6648989A JP2865698B2 JP 2865698 B2 JP2865698 B2 JP 2865698B2 JP 1066489 A JP1066489 A JP 1066489A JP 6648989 A JP6648989 A JP 6648989A JP 2865698 B2 JP2865698 B2 JP 2865698B2
- Authority
- JP
- Japan
- Prior art keywords
- ifosfamide
- mesna
- weight
- solution
- injection
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229960004635 mesna Drugs 0.000 title claims abstract description 68
- 238000002360 preparation method Methods 0.000 title claims description 15
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 claims abstract description 70
- 229960001101 ifosfamide Drugs 0.000 claims abstract description 70
- XOGTZOOQQBDUSI-UHFFFAOYSA-M Mesna Chemical compound [Na+].[O-]S(=O)(=O)CCS XOGTZOOQQBDUSI-UHFFFAOYSA-M 0.000 claims abstract description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 21
- 235000010355 mannitol Nutrition 0.000 claims description 20
- 229930195725 Mannitol Natural products 0.000 claims description 14
- 239000000594 mannitol Substances 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000011261 inert gas Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 230000000274 adsorptive effect Effects 0.000 claims description 2
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 53
- 238000002347 injection Methods 0.000 description 39
- 239000007924 injection Substances 0.000 description 39
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 238000004108 freeze drying Methods 0.000 description 21
- 238000011049 filling Methods 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 229960001855 mannitol Drugs 0.000 description 13
- 238000001035 drying Methods 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 238000003860 storage Methods 0.000 description 11
- 238000001914 filtration Methods 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- 238000004090 dissolution Methods 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000008215 water for injection Substances 0.000 description 6
- 239000003708 ampul Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- -1 chloroethylamino Chemical group 0.000 description 4
- 238000011109 contamination Methods 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- 238000001802 infusion Methods 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 238000011146 sterile filtration Methods 0.000 description 4
- 230000001954 sterilising effect Effects 0.000 description 4
- 230000001580 bacterial effect Effects 0.000 description 3
- 230000003750 conditioning effect Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229940056193 ifosfamide / mesna Drugs 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052756 noble gas Inorganic materials 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 229960004397 cyclophosphamide Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000002158 endotoxin Substances 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- CBCIHIVRDWLAME-UHFFFAOYSA-N hexanitrodiphenylamine Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O CBCIHIVRDWLAME-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229940081374 ifosfamide 1000 mg Drugs 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000027939 micturition Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011045 prefiltration Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 125000005500 uronium group Chemical group 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
- A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Biochemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Control Of El Displays (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3809337.5 | 1988-03-19 | ||
| DE3809337 | 1988-03-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH024796A JPH024796A (ja) | 1990-01-09 |
| JP2865698B2 true JP2865698B2 (ja) | 1999-03-08 |
Family
ID=6350216
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1066489A Expired - Lifetime JP2865698B2 (ja) | 1988-03-19 | 1989-03-20 | イホスフアミド‐メスナ凍結乾燥調製物及びその製法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4959215A (fr) |
| EP (1) | EP0334083B1 (fr) |
| JP (1) | JP2865698B2 (fr) |
| AT (1) | ATE65402T1 (fr) |
| CA (1) | CA1326452C (fr) |
| DE (1) | DE58900183D1 (fr) |
| ES (1) | ES2040394T3 (fr) |
| FI (1) | FI89456C (fr) |
| GR (1) | GR3002377T3 (fr) |
| IE (1) | IE60721B1 (fr) |
| PT (1) | PT90030B (fr) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5252341A (en) * | 1990-07-16 | 1993-10-12 | Degussa Aktiengesellschaft | Tablets and granulates containing mesna as active substance |
| DE4122167A1 (de) * | 1990-07-16 | 1992-01-23 | Asta Pharma Ag | Tablette und granulat enthaltend als wirkstoff mesna |
| US5227373A (en) * | 1991-10-23 | 1993-07-13 | Bristol-Myers Squibb Co. | Lyophilized ifosfamide compositions |
| DE4233842A1 (de) * | 1992-10-08 | 1994-04-14 | Asta Medica Ag | Mesna Injektionslösungen |
| WO1995007083A1 (fr) * | 1993-09-10 | 1995-03-16 | F.H. Faulding & Co. Limited | Composition de lyophilisat d'ifosfamide |
| US5789000A (en) * | 1994-11-14 | 1998-08-04 | Bionumerik Pharmaceuticals, Inc. | Sterile aqueous parenteral formulations of cis-diammine dichloro platinum |
| DE19529057B4 (de) * | 1995-08-08 | 2007-12-13 | Baxter Healthcare S.A. | Ifosfamid-Lyophilisat-Zubereitungen |
| IT1284973B1 (it) * | 1996-10-11 | 1998-05-28 | A R D O Associazione Ricerca E | Uso del sodio 2-mercaptoetansolfonato (mesna) in chirurgia |
| US6613927B1 (en) | 2002-02-08 | 2003-09-02 | American Pharmaceutical Partners, Inc. | Sterile lyophilized ifosfamide and associated methods |
| WO2004022699A2 (fr) * | 2002-09-05 | 2004-03-18 | Bharat Serums And Vaccines Ltd. | Composition liquide stable d'oxazaphosphorine renfermant du mesna |
| WO2004050012A2 (fr) * | 2002-12-02 | 2004-06-17 | Bharat Serums And Vaccines Ltd | Compositions a base d'ifosfamide pour l'administration parenterale et leur procede de preparation |
| US20070192947A1 (en) * | 2003-07-10 | 2007-08-23 | Cylena Medical Technologies Inc. | Protective apparel with improved doffing |
| DK1667655T3 (da) * | 2003-10-01 | 2011-10-24 | Baxter Int | Ny anvendelse, farmaceutiske præparater og en fremgangsmåde til deres fremstilling |
| KR20070058608A (ko) * | 2004-09-13 | 2007-06-08 | 바라트 쎄럼스 앤드 백신스 리미티드 | 항미생물 방부 효능을 갖는 정맥 내 투여를 위한 안정한에멀젼 조성물 |
| US8436190B2 (en) | 2005-01-14 | 2013-05-07 | Cephalon, Inc. | Bendamustine pharmaceutical compositions |
| US8158152B2 (en) * | 2005-11-18 | 2012-04-17 | Scidose Llc | Lyophilization process and products obtained thereby |
| AR072777A1 (es) | 2008-03-26 | 2010-09-22 | Cephalon Inc | Formas solidas de clorhidrato de bendamustina |
| WO2010010383A1 (fr) * | 2008-07-21 | 2010-01-28 | Isis Innovation Limited | Traitement de l’obésité |
| EP2401285B1 (fr) * | 2009-02-24 | 2012-10-10 | Dekk-Tec, Inc. | Complexes des 4-hydroperoxy ifosfamide comme inhibiteur du carcinoma |
| PL2994062T3 (pl) * | 2013-05-07 | 2020-05-18 | Auxin Surgery Sa | Urządzenie do dysekcji wspomaganej chemicznie |
| EP3092009B1 (fr) | 2014-01-06 | 2019-08-14 | AuXin Surgery SA | Compositions de mesna lyophilisées |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0002495B1 (fr) * | 1977-12-14 | 1984-02-15 | Asta-Werke Aktiengesellschaft Chemische Fabrik | Composition à utiliser en thérapie cytostatique |
| DE3111428A1 (de) * | 1981-03-24 | 1982-10-07 | Asta-Werke Ag, Chemische Fabrik, 4800 Bielefeld | Oxazaphosphorin-4-thio-alkansulfonsaeuren und deren neutrale salze, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen |
| ZA851062B (en) * | 1984-03-01 | 1985-11-27 | Asta Werke Ag Chem Fab | Salts of oxazaphosphorine derivatives and process for their production |
| US4797388A (en) * | 1984-05-21 | 1989-01-10 | Cetus Corporation | Pharmaceutical compositions with galactitol as carrier |
| US4859452A (en) * | 1986-01-17 | 1989-08-22 | Board Of Regents, The University Of Texas System | Methods for the reduction of difluoromethylornithine associated toxicity |
| ES2036553T3 (es) * | 1986-10-07 | 1993-06-01 | Boehringer Mannheim Italia S.P.A. | Composiciones farmaceuticas que tienen actividad antineoplastica. |
| NO873860L (no) * | 1986-10-31 | 1988-05-02 | Asta Pharma Ag | Ifosfamid-lyofilisat og fremgangsmaate til deres fremstilling. |
-
1989
- 1989-03-04 AT AT89103844T patent/ATE65402T1/de not_active IP Right Cessation
- 1989-03-04 DE DE8989103844T patent/DE58900183D1/de not_active Expired - Lifetime
- 1989-03-04 ES ES198989103844T patent/ES2040394T3/es not_active Expired - Lifetime
- 1989-03-04 EP EP89103844A patent/EP0334083B1/fr not_active Expired - Lifetime
- 1989-03-16 CA CA000593900A patent/CA1326452C/fr not_active Expired - Lifetime
- 1989-03-16 IE IE85489A patent/IE60721B1/en not_active IP Right Cessation
- 1989-03-17 PT PT90030A patent/PT90030B/pt not_active IP Right Cessation
- 1989-03-17 FI FI891283A patent/FI89456C/fi not_active IP Right Cessation
- 1989-03-20 US US07/325,883 patent/US4959215A/en not_active Expired - Lifetime
- 1989-03-20 JP JP1066489A patent/JP2865698B2/ja not_active Expired - Lifetime
-
1991
- 1991-07-25 GR GR91401005T patent/GR3002377T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GR3002377T3 (en) | 1992-12-30 |
| JPH024796A (ja) | 1990-01-09 |
| DE58900183D1 (de) | 1991-08-29 |
| CA1326452C (fr) | 1994-01-25 |
| ES2040394T3 (es) | 1993-10-16 |
| PT90030A (pt) | 1989-11-10 |
| EP0334083A1 (fr) | 1989-09-27 |
| PT90030B (pt) | 1994-05-31 |
| FI891283A0 (fi) | 1989-03-17 |
| IE60721B1 (en) | 1994-08-10 |
| FI89456C (fi) | 1993-10-11 |
| ATE65402T1 (de) | 1991-08-15 |
| EP0334083B1 (fr) | 1991-07-24 |
| IE890854L (en) | 1989-09-19 |
| FI89456B (fi) | 1993-06-30 |
| US4959215A (en) | 1990-09-25 |
| FI891283A (fi) | 1989-09-20 |
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